US4197375A - Photodegradability of plastic polyolefins - Google Patents
Photodegradability of plastic polyolefins Download PDFInfo
- Publication number
- US4197375A US4197375A US05/968,886 US96888678A US4197375A US 4197375 A US4197375 A US 4197375A US 96888678 A US96888678 A US 96888678A US 4197375 A US4197375 A US 4197375A
- Authority
- US
- United States
- Prior art keywords
- polyisobutylene
- plastic
- polyolefin
- polyethylene
- polyolefins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 36
- 239000004033 plastic Substances 0.000 title claims abstract description 29
- 229920003023 plastic Polymers 0.000 title claims abstract description 29
- 229920002367 Polyisobutene Polymers 0.000 claims abstract description 28
- 238000001782 photodegradation Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 12
- -1 polyethylene Polymers 0.000 claims description 10
- 239000004698 Polyethylene Substances 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 description 12
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 11
- 229940024874 benzophenone Drugs 0.000 description 11
- 239000000654 additive Substances 0.000 description 6
- 239000003504 photosensitizing agent Substances 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- 239000002285 corn oil Substances 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920001083 polybutene Polymers 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical group O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0033—Additives activating the degradation of the macromolecular compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/16—Applications used for films
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/43—Promoting degradability of polymers
Definitions
- the present invention relates to photodegradable plastic polyolefin. More particularly, the invention relates to plastic polyolefin containing polyisobutylene as photosensitizer.
- Plastic polyolefins are widely used in the manufacture of many articles. Such articles of importance include disposable containers for food and drinks and the like and films for agricultural mulching.
- the plastic polyolefins usually degrade to some degree in the sunlight. This degradation is undesirable with articles of manufacture where durability is important, as in the case of artificial turf for playing fields.
- Various inhibitors such as the UV radiation absorbing agents, have been added to inhibit photodegradation. See, for instance, U.S. Pat. No. 3,429,841 describing the addition of 2-hydroxybenzophenone and oxidized polymeric wax to propylene polymer fibers as ultraviolet light absorbers.
- Pigments have been incorporated into plastic polyolefins, particularly with the use of dispersants such as mineral oil, polyethylene glycol, dioctylphthalate, polyisobutylene, or butyl stearate. See, for instance, U.S. Pat. No. 3,523,916 describing the admixing of pigments and polyolefin with butyl stearate or low molecular weight liquid polyisobutylene in amounts of from about 0.1 to 0.6 weight percent.
- dispersants such as mineral oil, polyethylene glycol, dioctylphthalate, polyisobutylene, or butyl stearate.
- a method for improving photodegradability of plastic polyolefin compositions which comprises physically contacting plastic polyolefin compositions which are resistant to photodegradation with a minor proportion of polyisobutylene sufficient to accelerate the photodegradation of the plastic polyolefin, said polyisobutylene having a number average molecular weight of from about 400 to about 900, preferably about 400 to about 700.
- the improved plastic polyolefin compositions of the invention and articles thereof degrade upon exposure to sunlight over a determinable period of time, as desired, thereby facilitating their disposal.
- plastic polyolefins of the compositions according to the present invention are well known for their use in the molding and casting of articles such as containers and films. Included are high and low density polyethylene, polypropylene, poly-1-butene, polystyrene, and ethylene copolymers, mixtures of polyethylene and polypropylene, as well as mixtures of the aforementioned polyolefins, and the like. Such polyolefins are normally solid.
- the plastic polyolefin and polyisobutylene are brought into physical contact and combined in various ways.
- the plastic polyolefin is conveniently melted and mixed with the polyisobutylene with the aid of a conventional mixer of the Banbury type.
- the polyisobutylene is also readily added to the plastic polyolefin during other manufacturing operations as, for example, in the use of screw extruders.
- a preferred aspect of the improved photodegradable plastic polyolefin compositions of the invention resides in the fact that the polyisobutylene photosensitizer may be applied in the appropriate amounts to the surface of the article of manufacture.
- the polyisobutylene penetrates the surface and provides the desired degree of photodegradability.
- the polyisobutylene photosensitizer may be dissolved in conventional solvents such as petroleum hydrocarbon thinner. Preferably, such solvents evaporate at about room temperature and leave little or no residue other than the polyisobutylene.
- the improved plastic polyolefin compositions in accordance with the invention may contain other conventional additives. Included are pigments, antioxidants, plasticizers, etc. Other photosensitizers are also included, such as the benzophenones.
- the polyisobutylene photosensitizer is readily characterized by its number average molecular weight, as mentioned above.
- Such polyisobutylenes are normally liquid and are commonly produced by catalytic polymerization of an isobutylene-rich stream.
- the preferred polyisobutylenes are also characterized by their viscosities, which range from about 500 to 6,000 SSU at 100° F. and from about 60 to 300 SSU at 210° F.
- the polyisobutylenes are sold by Chevron Chemical Company as Chevron Polybutenes and are designated according to their "Polybutene Grade" as shown in the following table:
- polyisobutylenes having a number average molecular weight of from about 400 to about 900 are most preferred since they provide a desired degree of photodegradability of polyethylene, a preferred embodiment of the invention.
- polyisobutylenes as well as other additives are combined with the plastic polyolefins in the compositions of the invention in any amounts sufficient to accelerate the photodegradation of the polyolefin and provide the desired amount of decomposition along with other physical characteristics. Ordinarily from about 1 to 3% by weight of the polyisobutylene is used based on the plastic polyolefin.
- the photodegradable plastic polyolefin compositions of the invention are illustrated by the following examples.
- a 2-mil commercial polyethylene film was treated with solutions of the additives in petroleum hydrocarbon thinner. After the thinner evaporated, the film was stored inside at 100° F. for 30 days to allow the additives to diffuse into the film prior to outdoor exposure.
- the 5% solutions provide about 1% by weight of polyisobutylene in the plastic polyolefin.
- the degradability of the treated polyolefin was evaluated by testing for elongation using an Instron machine in accordance with the general test method outlined in ASTM D-882. The results of the various examples are summarized in the following table:
Abstract
Plastic polyolefins which are resistant to photodegradation are combined with polyisobutylene to improve photodegradability.
Description
This application is a continuation-in-part of application Ser. No. 859,776, filed Dec. 12, 1977 now abandoned.
1. Field of the Invention
The present invention relates to photodegradable plastic polyolefin. More particularly, the invention relates to plastic polyolefin containing polyisobutylene as photosensitizer.
2. Description of the Prior Art
Plastic polyolefins are widely used in the manufacture of many articles. Such articles of importance include disposable containers for food and drinks and the like and films for agricultural mulching.
The plastic polyolefins usually degrade to some degree in the sunlight. This degradation is undesirable with articles of manufacture where durability is important, as in the case of artificial turf for playing fields. Various inhibitors, such as the UV radiation absorbing agents, have been added to inhibit photodegradation. See, for instance, U.S. Pat. No. 3,429,841 describing the addition of 2-hydroxybenzophenone and oxidized polymeric wax to propylene polymer fibers as ultraviolet light absorbers.
However, in the case of plastic polyolefins for disposable containers and agricultural mulching films and the like it is ecologically desirable to get rid of the used containers and mulching film. Photosensitizers have been added to the plastic polyolefins to accelerate degradation on exposure to sunlight, thereby facilitating the disposal of the plastic polyolefin articles. See, for instance, U.S. Pat. No. 4,038,227 describing the use of benzophenone and other additives to promote the degradation of polyolefins and U.S. Pat. No. 3,679,777 describing the use of gamma-pyrone ring-containing compound to accelerate the photodegradability of polyolefins.
Pigments have been incorporated into plastic polyolefins, particularly with the use of dispersants such as mineral oil, polyethylene glycol, dioctylphthalate, polyisobutylene, or butyl stearate. See, for instance, U.S. Pat. No. 3,523,916 describing the admixing of pigments and polyolefin with butyl stearate or low molecular weight liquid polyisobutylene in amounts of from about 0.1 to 0.6 weight percent.
In accordance with the present invention there is provided a method for improving photodegradability of plastic polyolefin compositions which comprises physically contacting plastic polyolefin compositions which are resistant to photodegradation with a minor proportion of polyisobutylene sufficient to accelerate the photodegradation of the plastic polyolefin, said polyisobutylene having a number average molecular weight of from about 400 to about 900, preferably about 400 to about 700.
The improved plastic polyolefin compositions of the invention and articles thereof degrade upon exposure to sunlight over a determinable period of time, as desired, thereby facilitating their disposal.
The plastic polyolefins of the compositions according to the present invention are well known for their use in the molding and casting of articles such as containers and films. Included are high and low density polyethylene, polypropylene, poly-1-butene, polystyrene, and ethylene copolymers, mixtures of polyethylene and polypropylene, as well as mixtures of the aforementioned polyolefins, and the like. Such polyolefins are normally solid.
The plastic polyolefin and polyisobutylene are brought into physical contact and combined in various ways. The plastic polyolefin is conveniently melted and mixed with the polyisobutylene with the aid of a conventional mixer of the Banbury type. The polyisobutylene is also readily added to the plastic polyolefin during other manufacturing operations as, for example, in the use of screw extruders.
A preferred aspect of the improved photodegradable plastic polyolefin compositions of the invention resides in the fact that the polyisobutylene photosensitizer may be applied in the appropriate amounts to the surface of the article of manufacture. The polyisobutylene penetrates the surface and provides the desired degree of photodegradability. For convenience of application, the polyisobutylene photosensitizer may be dissolved in conventional solvents such as petroleum hydrocarbon thinner. Preferably, such solvents evaporate at about room temperature and leave little or no residue other than the polyisobutylene.
The improved plastic polyolefin compositions in accordance with the invention may contain other conventional additives. Included are pigments, antioxidants, plasticizers, etc. Other photosensitizers are also included, such as the benzophenones.
The polyisobutylene photosensitizer is readily characterized by its number average molecular weight, as mentioned above. Such polyisobutylenes are normally liquid and are commonly produced by catalytic polymerization of an isobutylene-rich stream. The preferred polyisobutylenes are also characterized by their viscosities, which range from about 500 to 6,000 SSU at 100° F. and from about 60 to 300 SSU at 210° F. The polyisobutylenes are sold by Chevron Chemical Company as Chevron Polybutenes and are designated according to their "Polybutene Grade" as shown in the following table:
TABLE I
__________________________________________________________________________
Polybutene (PB) Grade
Physical Properties
Test Method
6 8 12 16 18 22 24 32 122 128
__________________________________________________________________________
Number Average
Molecular Weight
Mechro Osmometer
SM-180-6
330
440
530
640
730
800
950
1,400
2,500
2,700
Viscosity @
ASTM D-445
100° F., SSU
& D-446
134
560
3,400
5,700
9,500
16,500
40,000
123,000
715,000
890,000
Viscosity @
ASTM D-445
210° F., SSU
& D-446
41
63
163
250
350
550
1,050
2,990
15,800
19,500
__________________________________________________________________________
For present purposes the polyisobutylenes having a number average molecular weight of from about 400 to about 900 are most preferred since they provide a desired degree of photodegradability of polyethylene, a preferred embodiment of the invention.
The polyisobutylenes as well as other additives are combined with the plastic polyolefins in the compositions of the invention in any amounts sufficient to accelerate the photodegradation of the polyolefin and provide the desired amount of decomposition along with other physical characteristics. Ordinarily from about 1 to 3% by weight of the polyisobutylene is used based on the plastic polyolefin.
The photodegradable plastic polyolefin compositions of the invention are illustrated by the following examples. In these examples a 2-mil commercial polyethylene film was treated with solutions of the additives in petroleum hydrocarbon thinner. After the thinner evaporated, the film was stored inside at 100° F. for 30 days to allow the additives to diffuse into the film prior to outdoor exposure. The 5% solutions provide about 1% by weight of polyisobutylene in the plastic polyolefin. The degradability of the treated polyolefin was evaluated by testing for elongation using an Instron machine in accordance with the general test method outlined in ASTM D-882. The results of the various examples are summarized in the following table:
TABLE II
__________________________________________________________________________
ELONGATION OF TREATED 2 MIL
POLYETHYLENE FILMS
Maximum Elongation of Treated Film, %
Stored Stored
Inside Inside
30 Days at
30 Days at
Stored
100° F. and
100° F. and
Inside
120 Days at
Exposed
Example Freshly
30 Days
Room Outside
No. Treatment.sup.1
Prepared
at 100° F.
Temperature
120 Days.sup.2
__________________________________________________________________________
1 None 385 420 300 235,
160
2 Hydrocarbon Paint
Thinner 365 395 495 200,
150
3 Benzophenone (1%)
365 355 505 10,
15
4 PB-8 (5%) 385 390 410 10,
20
5 PB-8 (5%) +
375 335 425 10,
10
Benzophenone (1%)
6 PB-16 (5%) 410 375 350 20,
15
7 PB-16 (5%) +
345 355 480 25,
15
Benzophenone (1%)
8 PB-32 (5%) 375 360 460 20,
15
9 PB-32 (5%) +
355 390 525 80,
20
Benzophenone (1%)
10 PB-128 (5%)
330 305 480 40,
45
11 PB-128 (5%) +
330 395 515 20,
15
Benzophenone (1%)
12 Corn Oil 23
395 350 465 60,
56
(5%)
13 Corn Oil 23
360 300 430 10,
15
(5%) + Benzo-
phenone (1%)
14 Corn Oil (5%)
385 330 505 65,
40
15 Corn Oil (5%)
375 365 495 10,
10
+ Benzophenone
(1%)
16 α-Olefin C.sub.8 -C.sub.9
385 410 435 195,
220
(5%)
17 α-Olefin C.sub.8 -C.sub.9
290 375 540 10,
15
(5%) + Benzo-
phenone (1%)
18 α-Olefin C.sub.13 -C.sub.14
385 405 450 135,
105
(5%)
19 α-Olefin C.sub.13 -C.sub.14
370 390 375 10,
55
(5%) + Benzo-
phenone (1%)
20 α-Olefin C.sub.15 -C.sub.20
280 375 482 25,
80
(5%)
21 α-Olefin C.sub.15 -C.sub.20
250 435 460 15,
10
(5%) + Benzo-
phenone (1%)
__________________________________________________________________________
.sup.1 The number in parentheses after the additive is its concentration
in the hydrocarbon paint thinner solution used to treat the film.
.sup.2 Duplicate samples.
The above test results show that the low molecular weight polyisobutylenes were particularly effective as indicated by the experiments using PB-8 and PB-16.
While the character of this invention has been described in detail with numerous examples, this has been done by way of illustration only and without limitation of the invention. It will be apparent to those skilled in the art that modifications and variations of the illustrative examples may be made in the practice of the invention within the scope of the following claims.
Claims (5)
1. A method for improving photodegradability of plastic polyolefin compositions which comprises physically contacting plastic polyolefin compositions which are resistant to photodegradation with a minor proportion of polyisobutylene sufficient to accelerate the photodegradation of the plastic polyolefin, said polyisobutylene having a number average molecular weight of from about 400 to about 900.
2. A method according to claim 1 wherein the polyisobutylene has a number average molecular weight of from about 400 to about 700.
3. A method according to claim 1 wherein the polyolefin is polyethylene.
4. A method according to claim 3 wherein the polyisobutylene is applied to the surface of the plastic polyethylene by dipping said polyethylene into a hydrocarbon solution of the polyisobutylene.
5. A method according to claim 4 wherein the polyisobutylene is present on the surface of the plastic polyolefin in an amount from about 1 to 3 percent by weight based on the polyethylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/968,886 US4197375A (en) | 1977-12-12 | 1978-12-13 | Photodegradability of plastic polyolefins |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85977677A | 1977-12-12 | 1977-12-12 | |
| US05/968,886 US4197375A (en) | 1977-12-12 | 1978-12-13 | Photodegradability of plastic polyolefins |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US85977677A Continuation-In-Part | 1977-12-12 | 1977-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4197375A true US4197375A (en) | 1980-04-08 |
Family
ID=27127538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/968,886 Expired - Lifetime US4197375A (en) | 1977-12-12 | 1978-12-13 | Photodegradability of plastic polyolefins |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4197375A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4571329A (en) * | 1984-08-13 | 1986-02-18 | Babcock-Hitachi Kabushiki Kaisha | Ammonia reduction-denitration process and apparatus therefor |
| US5145732A (en) * | 1989-03-01 | 1992-09-08 | Osaka Gas Company Limited | High bulk density carbon fiber felt and thermal insulator |
| USH1120H (en) | 1991-10-31 | 1992-12-01 | Shell Oil Company | Polybutylene in recyclable material streams |
| US5204174A (en) * | 1990-05-04 | 1993-04-20 | Kimberly-Clark Corporation | Fine fiber webs with improved physical properties |
| US5518730A (en) | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| US20070231191A1 (en) * | 2006-03-31 | 2007-10-04 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Methods and systems for monitoring sterilization status |
| US20070231189A1 (en) * | 2006-03-31 | 2007-10-04 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Sterilization methods and systems |
| US20070231204A1 (en) * | 2006-03-31 | 2007-10-04 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Surveying sterilizer methods and systems |
| US20070231192A1 (en) * | 2006-03-31 | 2007-10-04 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Sterilization methods and systems |
| US20070286398A1 (en) * | 2006-06-07 | 2007-12-13 | Venkatesan Ramamoorthy | Voice Recognition Dialing For Alphabetic Phone Numbers |
| US20090036566A1 (en) * | 2007-07-30 | 2009-02-05 | City University Of Hong Kong | Biodegradable composite, product made therefrom, and method of manufacture thereof |
| US20090208378A1 (en) * | 2006-03-31 | 2009-08-20 | Searete Llc | Methods and systems for monitoring sterilization status |
| US20100111775A1 (en) * | 2006-03-31 | 2010-05-06 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Surveying sterilizer methods and systems |
| CN103834084A (en) * | 2014-03-06 | 2014-06-04 | 苏州天兼新材料科技有限公司 | Environment-friendly modified high-polymer new material capable of initiating multiple degradation and preparation method thereof |
| US8758679B2 (en) | 2006-03-31 | 2014-06-24 | The Invention Science Fund I, Llc | Surveying sterilizer methods and systems |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3523916A (en) * | 1967-01-26 | 1970-08-11 | Phillips Petroleum Co | Additive dispersant |
| US3797690A (en) * | 1971-12-08 | 1974-03-19 | Owens Illinois Inc | Preparation of degradable polymeric material |
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1978
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3523916A (en) * | 1967-01-26 | 1970-08-11 | Phillips Petroleum Co | Additive dispersant |
| US3797690A (en) * | 1971-12-08 | 1974-03-19 | Owens Illinois Inc | Preparation of degradable polymeric material |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4571329A (en) * | 1984-08-13 | 1986-02-18 | Babcock-Hitachi Kabushiki Kaisha | Ammonia reduction-denitration process and apparatus therefor |
| US5145732A (en) * | 1989-03-01 | 1992-09-08 | Osaka Gas Company Limited | High bulk density carbon fiber felt and thermal insulator |
| US5204174A (en) * | 1990-05-04 | 1993-04-20 | Kimberly-Clark Corporation | Fine fiber webs with improved physical properties |
| USH1120H (en) | 1991-10-31 | 1992-12-01 | Shell Oil Company | Polybutylene in recyclable material streams |
| US5518730A (en) | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| US20090208378A1 (en) * | 2006-03-31 | 2009-08-20 | Searete Llc | Methods and systems for monitoring sterilization status |
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| US7754156B2 (en) | 2006-03-31 | 2010-07-13 | The Invention Science Fund I, Llc | Surveying sterilizer methods and systems |
| US8114342B2 (en) | 2006-03-31 | 2012-02-14 | The Invention Science Fund I, Llc | Methods and systems for monitoring sterilization status |
| US8178042B2 (en) | 2006-03-31 | 2012-05-15 | The Invention Science Fund I, Llc | Methods and systems for monitoring sterilization status |
| US20070231189A1 (en) * | 2006-03-31 | 2007-10-04 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Sterilization methods and systems |
| US8992837B2 (en) | 2006-03-31 | 2015-03-31 | The Invention Science Fund I, Llc | Methods and systems for monitoring sterilization status |
| US8758679B2 (en) | 2006-03-31 | 2014-06-24 | The Invention Science Fund I, Llc | Surveying sterilizer methods and systems |
| US8932535B2 (en) | 2006-03-31 | 2015-01-13 | The Invention Science Fund I, Llc | Surveying sterilizer methods and systems |
| US20070286398A1 (en) * | 2006-06-07 | 2007-12-13 | Venkatesan Ramamoorthy | Voice Recognition Dialing For Alphabetic Phone Numbers |
| US20090036566A1 (en) * | 2007-07-30 | 2009-02-05 | City University Of Hong Kong | Biodegradable composite, product made therefrom, and method of manufacture thereof |
| CN103834084A (en) * | 2014-03-06 | 2014-06-04 | 苏州天兼新材料科技有限公司 | Environment-friendly modified high-polymer new material capable of initiating multiple degradation and preparation method thereof |
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